Not that long ago, Michelangelo "Mike" Volpi, 42, was one of the most important people in Silicon Valley. At Cisco Systems, he was the golden boy who was instrumental in the company's acquisition strategy and rumored to be in line to eventually succeed John Chambers as CEO.

Volpi surprised the tech world by walking away in December 2007, falling off the valley's radar. Until now. In early September, he helped orchestrate the winning bid to acquire Skype from eBay. But his triumphant return to the valley's dealmaking spotlight took an ugly turn.

Volpi is now enmeshed in a legal swamp over his role in assembling a consortium of private investors to buy Skype in a deal worth $2.75 billion. It turns out that while Volpi was putting together this bid, he was working as CEO for another startup called Joost, whose founders were also interested in buying Skype.

And who were those Joost founders? Why, that would be Janus Friis and Niklas Zennström, the two people who founded Skype, sold it to eBay in 2005, and now want to buy it back.

Joost has sued Volpi and his venture capital firm, Index Ventures, in a Delaware federal court, one of three separate but related lawsuits plaguing the Skype deal. Whether the Joost founders have legitimate legal claims, or whether this is all about retribution against Volpi, we'll have to wait and see. But in the meantime, the messy entrails of the deal are spilling into plain view through the mounting pile of legal paperwork. The latest filings in the Delaware case, for instance, include several e-mails apparently sent by Volpi using his Joost account as he was putting together the deal, with critical references to both his bosses at the time, as well as some of his future partners in the Joost deal.

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Even if we give Volpi the benefit of the doubt and assume he prevails on the legal issues, his actions and behavior are likely to put a considerable dent in his reputation. It may be hard to predict who will be the winner in these legal cases, but it's clear that Volpi is the early loser.

When contacted for this column, an Index spokesperson, speaking on behalf of both Volpi and Index, provided the following statement:

"This filing reflects a continued series of public attacks that are guided by personal agendas rather than substantive legal fact. We will continue to counter this transparent agenda aggressively in the court system."

Let's flash back for a moment, just to understand Volpi's considerable reputation in the valley. Born in Italy, he joined Cisco in his late 20s, and by age 31, was a key player in Cisco's acquisition strategy. In a 1998 profile, The New York Times called Volpi Cisco's "whiz kid" and said he was "among the most influential deal makers in technology." In his latest bio, Volpi takes credit for about 70 Cisco purchases.

When Volpi announced his departure from Cisco in December 2007, such was his reputation that there were even some whispers about whether Chambers was overstaying his tenure.

A few weeks later, Joost, based in London, announced it had hired Volpi as CEO. Joost was a video portal that represented the first big venture by Friis and Zennström since selling Skype to eBay.

But Volpi's first CEO outing fizzled badly, as rivals like Hulu built bigger followings and partnerships with TV and movie studios.

As Joost stumbled, Volpi was stitching together a bid for Skype, which eBay was looking to unload, and discussing his own potential move to Index Ventures, a venture capital firm in London. In one e-mail filed by Joost in the Delaware case, dated Feb. 23, 2009, Volpi discussed the Skype bid with Danny Rimer, an Index partner. The Volpi e-mail refers to various people who might be involved, and Volpi's desire to possibly be chairman of the new Skype.

"Could be cool," Volpi writes at the end. "J/N/Dyne will be very unhappy, but ... oh well."

In this case, J/N are Janus Friis and Niklas Zennström, and Mark Dyne is a Los Angeles banker who was a former Skype board member. Oh well, indeed.

The e-mails continued for several months. Volpi announced he was leaving Joost at the end of June. A couple of weeks later, he joined Index Ventures. On Sept. 1, eBay said that a group including Index, Silver Lake Partners, Marc Andreessen and the Canada Pension Plan Investment Board had agreed to buy 65 percent of Skype for about $1.9 billion.

This is a pretty esteemed group. And it's worth noting, too, that Volpi has always had a reputation as one of the good guys. A couple of people I talked to who knew him during his Cisco days said his role in all of this seemed out of character.

First, if the Internet has taught us anything, it's that you don't use company e-mail to do sneaky things. Volpi appears to have sent all these e-mails contained in the case file using his Joost e-mail account, conveniently leaving behind copies on the server. It's hard to believe that someone involved in so many corporate acquisitions would be so careless.

As Rimer wrote in an e-mail to Volpi on May 13: "Let's discuss this later and btw, we should use your perso[nal] address for this ;)" Good idea.

Even worse, Volpi seems to have grotesquely underestimated how upset the Joost founders would be. In case you're wondering, the answer appears to be: VERY ANGRY.

Volpi must have known them personally. And he would have also known that Friis and Zennström were the founders of Kazaa, the peer-to-peer music-sharing service that was hounded in court for years by the music business. These are two guys who know their way around a legal brief, have a taste for litigation, and know how to use the courts as a blunt-force instrument. They're not usually the guys you want to poke with a stick. Did Volpi really think they weren't going to fight back?

Volpi's greatest miscalculation, however, may have been not realizing how all this would look should it see the light of day.

On a purely legal basis, the question of whether Volpi violated any fiduciary duties to Joost are far from clear. Friis and Zennström wanted to bid on Skype for themselves, not on behalf of Joost. They also accuse Volpi of wanting to poach some Joost employees and technology to use at Skype, but that's a murky issue.

But it's fair to say that Volpi didn't show a whole lot of loyalty to the guys who hired him. Was he legally required to do so? Hard to say, according to the experts I consulted. But does it make me want to do a business deal with Volpi? Not really. It makes me wonder how all this is being viewed by Volpi's new partners in the Skype acquisition.

"I totally get that it's Egon's deal," Volpi wrote in an e-mail to Rimer on May 13, referring to Egon Durban of Silver Lake Partners. "I didn't like him that much, but happy to develop the relationship there." Volpi also said he and current Skype president Josh Silverman could "bond on the 'clean up after nik/jan' theme."

Best case for Volpi, those e-mails make for some awkward board meetings. Worst case, Volpi's play for an Internet telephone empire makes him someone who can't get his calls returned.